AU2015341779B2 - Synthesis of copanlisib and its dihydrochloride salt - Google Patents
Synthesis of copanlisib and its dihydrochloride salt Download PDFInfo
- Publication number
- AU2015341779B2 AU2015341779B2 AU2015341779A AU2015341779A AU2015341779B2 AU 2015341779 B2 AU2015341779 B2 AU 2015341779B2 AU 2015341779 A AU2015341779 A AU 2015341779A AU 2015341779 A AU2015341779 A AU 2015341779A AU 2015341779 B2 AU2015341779 B2 AU 2015341779B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- compound
- solvent
- copanlisib
- base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- PZBCKZWLPGJMAO-UHFFFAOYSA-N COc(c1c(cc2)C3=NCCN3C(NC(c3cnc(N)nc3)=O)=N1)c2OCCCN1CCOCC1 Chemical compound COc(c1c(cc2)C3=NCCN3C(NC(c3cnc(N)nc3)=O)=N1)c2OCCCN1CCOCC1 PZBCKZWLPGJMAO-UHFFFAOYSA-N 0.000 description 3
- PHCNQUJHXJQLQR-UHFFFAOYSA-N COc(c(O)ccc1C=O)c1[N+]([O-])=O Chemical compound COc(c(O)ccc1C=O)c1[N+]([O-])=O PHCNQUJHXJQLQR-UHFFFAOYSA-N 0.000 description 2
- AZZZZPCGUSXSOF-UHFFFAOYSA-N COc(c(N=O)c(C=O)cc1)c1OCCCN1CCOCC1 Chemical compound COc(c(N=O)c(C=O)cc1)c1OCCCN1CCOCC1 AZZZZPCGUSXSOF-UHFFFAOYSA-N 0.000 description 1
- ZYVGMXTZLDVOIW-UHFFFAOYSA-N COc(c(OCCCN1CCOCC1)ccc12)c1N=C(N)N1C2=NCC1 Chemical compound COc(c(OCCCN1CCOCC1)ccc12)c1N=C(N)N1C2=NCC1 ZYVGMXTZLDVOIW-UHFFFAOYSA-N 0.000 description 1
- ZROYKUBDBPTBSM-UHFFFAOYSA-N COc(c(OCCCN1CCOCC1)ccc1C2=NCCN2)c1N Chemical compound COc(c(OCCCN1CCOCC1)ccc1C2=NCCN2)c1N ZROYKUBDBPTBSM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14192202.1A EP3018131A1 (en) | 2014-11-07 | 2014-11-07 | Synthesis of copanlisib and its dihydrochloride salt |
| EP14192202.1 | 2014-11-07 | ||
| PCT/EP2015/075765 WO2016071426A1 (en) | 2014-11-07 | 2015-11-05 | Synthesis of copanlisib and its dihydrochloride salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2015341779A1 AU2015341779A1 (en) | 2017-05-11 |
| AU2015341779B2 true AU2015341779B2 (en) | 2020-02-27 |
Family
ID=51866060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2015341779A Active AU2015341779B2 (en) | 2014-11-07 | 2015-11-05 | Synthesis of copanlisib and its dihydrochloride salt |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US10035803B2 (hr) |
| EP (2) | EP3018131A1 (hr) |
| JP (1) | JP6691114B2 (hr) |
| KR (1) | KR102562286B1 (hr) |
| CN (1) | CN107074776B (hr) |
| AR (1) | AR102568A1 (hr) |
| AU (1) | AU2015341779B2 (hr) |
| BR (1) | BR112017009471B1 (hr) |
| CA (1) | CA2966796C (hr) |
| CL (1) | CL2017001130A1 (hr) |
| CO (1) | CO2017004533A2 (hr) |
| DK (1) | DK3215507T3 (hr) |
| EA (1) | EA031248B1 (hr) |
| ES (1) | ES2716730T3 (hr) |
| HR (1) | HRP20190527T8 (hr) |
| HU (1) | HUE042794T2 (hr) |
| IL (1) | IL251586B (hr) |
| JO (1) | JO3487B1 (hr) |
| LT (1) | LT3215507T (hr) |
| MX (1) | MX365111B (hr) |
| MY (1) | MY183123A (hr) |
| NZ (1) | NZ730843A (hr) |
| PE (1) | PE20170951A1 (hr) |
| PL (1) | PL3215507T3 (hr) |
| PT (1) | PT3215507T (hr) |
| RS (1) | RS58494B1 (hr) |
| SG (1) | SG11201702999XA (hr) |
| SI (1) | SI3215507T1 (hr) |
| TR (1) | TR201904346T4 (hr) |
| TW (1) | TWI697494B (hr) |
| UA (1) | UA118999C2 (hr) |
| UY (1) | UY36396A (hr) |
| WO (1) | WO2016071426A1 (hr) |
| ZA (1) | ZA201703866B (hr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2168583A1 (en) | 2008-09-24 | 2010-03-31 | Bayer Schering Pharma Aktiengesellschaft | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma |
| EP2508525A1 (en) | 2011-04-05 | 2012-10-10 | Bayer Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts |
| AP2015008750A0 (en) | 2013-04-08 | 2015-09-30 | Bayer Pharma AG | Use of substituted 2,3-dihydroimidazo[1,2-c] quinazolines for treating lymphomas |
| EP3018127A1 (en) | 2014-11-07 | 2016-05-11 | Bayer Pharma Aktiengesellschaft | Synthesis of copanlisib and its dihydrochloride salt |
| US10406162B2 (en) | 2015-03-09 | 2019-09-10 | Bayer Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-C]quinazoline-containing combinations |
| CN105130998B (zh) * | 2015-09-25 | 2017-07-28 | 苏州立新制药有限公司 | 库潘尼西的制备方法 |
| CN108884098B (zh) | 2016-03-08 | 2021-09-14 | 拜耳制药股份公司 | 2-氨基-N-[7-甲氧基-2,3-二氢咪唑并[1,2-c]喹唑啉-5-基]嘧啶-5-甲酰胺类 |
| WO2018054782A1 (en) | 2016-09-23 | 2018-03-29 | Bayer Pharma Aktiengesellschaft | Combination of pi3k-inhibitors |
| US11185549B2 (en) | 2017-06-28 | 2021-11-30 | Bayer Consumer Care Ag | Combination of a PI3K-inhibitor with an androgen receptor antagonist |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008070150A1 (en) * | 2006-12-05 | 2008-06-12 | Bayer Schering Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline derivatives useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1319674B1 (it) * | 2000-12-01 | 2003-10-23 | Erregierre Spa | Processo per la preparazione dell'acido1-(aminometil)cicloesanacetico. |
| TW565582B (en) * | 2001-04-13 | 2003-12-11 | Kaneka Corp | Diamine, acid dianhydride, and reactive group containing polyimide composition prepared therefrom and preparing them |
| MXPA04001286A (es) * | 2001-08-15 | 2004-05-27 | Du Pont | Arilamidas orto-heterociclicas sustituidas para controlar plagas de invertebrados. |
| NZ539062A (en) | 2002-09-30 | 2007-05-31 | Bayer Pharmaceuticals Corp | Fused azole-pyrimidine derivatives exhibiting enhanced potency for phosphotidylinositol-3-kinase (P13K) inhibition |
| JP5620275B2 (ja) * | 2008-01-14 | 2014-11-05 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 超増殖性疾患及び脈管形成に関連する疾病を処理するために有用なスルホン置換された２，３−ジヒドロイミダゾ［１，２−ｃ］キナゾリン誘導体類 |
| EP2496575B1 (en) | 2009-11-04 | 2014-04-30 | Novartis AG | Heterocyclic sulfonamide derivatives useful as mek inhibitors |
| EP2508525A1 (en) * | 2011-04-05 | 2012-10-10 | Bayer Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts |
-
2014
- 2014-11-07 EP EP14192202.1A patent/EP3018131A1/en not_active Withdrawn
-
2015
- 2015-05-11 UA UAA201705431A patent/UA118999C2/uk unknown
- 2015-11-03 JO JOP/2015/0273A patent/JO3487B1/ar active
- 2015-11-05 PT PT15790141T patent/PT3215507T/pt unknown
- 2015-11-05 PL PL15790141T patent/PL3215507T3/pl unknown
- 2015-11-05 NZ NZ730843A patent/NZ730843A/en unknown
- 2015-11-05 EP EP15790141.4A patent/EP3215507B1/en active Active
- 2015-11-05 MY MYPI2017701571A patent/MY183123A/en unknown
- 2015-11-05 DK DK15790141.4T patent/DK3215507T3/en active
- 2015-11-05 CA CA2966796A patent/CA2966796C/en active Active
- 2015-11-05 EA EA201790982A patent/EA031248B1/ru not_active IP Right Cessation
- 2015-11-05 SI SI201530660T patent/SI3215507T1/sl unknown
- 2015-11-05 CN CN201580059995.1A patent/CN107074776B/zh active Active
- 2015-11-05 RS RS20190398A patent/RS58494B1/sr unknown
- 2015-11-05 MX MX2017005891A patent/MX365111B/es active IP Right Grant
- 2015-11-05 SG SG11201702999XA patent/SG11201702999XA/en unknown
- 2015-11-05 AU AU2015341779A patent/AU2015341779B2/en active Active
- 2015-11-05 BR BR112017009471-1A patent/BR112017009471B1/pt active IP Right Grant
- 2015-11-05 WO PCT/EP2015/075765 patent/WO2016071426A1/en active Application Filing
- 2015-11-05 TR TR2019/04346T patent/TR201904346T4/tr unknown
- 2015-11-05 HU HUE15790141A patent/HUE042794T2/hu unknown
- 2015-11-05 LT LTEP15790141.4T patent/LT3215507T/lt unknown
- 2015-11-05 JP JP2017523873A patent/JP6691114B2/ja active Active
- 2015-11-05 KR KR1020177011704A patent/KR102562286B1/ko active IP Right Grant
- 2015-11-05 US US15/524,478 patent/US10035803B2/en active Active
- 2015-11-05 ES ES15790141T patent/ES2716730T3/es active Active
- 2015-11-05 PE PE2017000848A patent/PE20170951A1/es unknown
- 2015-11-06 AR ARP150103617A patent/AR102568A1/es unknown
- 2015-11-06 UY UY0001036396A patent/UY36396A/es not_active Application Discontinuation
- 2015-11-06 TW TW104136727A patent/TWI697494B/zh active
-
2017
- 2017-04-05 IL IL251586A patent/IL251586B/en active IP Right Grant
- 2017-05-05 CL CL2017001130A patent/CL2017001130A1/es unknown
- 2017-05-05 CO CONC2017/0004533A patent/CO2017004533A2/es unknown
- 2017-06-06 ZA ZA2017/03866A patent/ZA201703866B/en unknown
-
2019
- 2019-03-18 HR HRP20190527TT patent/HRP20190527T8/hr unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008070150A1 (en) * | 2006-12-05 | 2008-06-12 | Bayer Schering Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline derivatives useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |